WO2005007664A1 - COMPOSE DE 3-$G(A)-GLYCOSYLE$G(A), $G(A)-TETRALOSE, METHODE DE FABRICATION ET UTILISATION - Google Patents

COMPOSE DE 3-$G(A)-GLYCOSYLE$G(A), $G(A)-TETRALOSE, METHODE DE FABRICATION ET UTILISATION Download PDF

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WO2005007664A1
WO2005007664A1 PCT/JP2004/010225 JP2004010225W WO2005007664A1 WO 2005007664 A1 WO2005007664 A1 WO 2005007664A1 JP 2004010225 W JP2004010225 W JP 2004010225W WO 2005007664 A1 WO2005007664 A1 WO 2005007664A1
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Prior art keywords
trehalose
chemical formula
glycosyl
producing
bond
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PCT/JP2004/010225
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English (en)
Japanese (ja)
Inventor
Tomoyuki Nishimoto
Hikaru Watanabe
Shigeharu Fukuda
Toshio Miyake
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Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
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Priority to GB0603159A priority Critical patent/GB2420345B/en
Priority to US10/565,083 priority patent/US20060183714A1/en
Publication of WO2005007664A1 publication Critical patent/WO2005007664A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • A23G3/42—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/10—Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/385—Concentrates of non-alcoholic beverages
    • A23L2/39—Dry compositions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/702—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations

Definitions

  • the present invention relates to novel carbohydrates 3_-glycosyl spikes, hy-trehaloses and methods for producing the same, and uses thereof.
  • the present invention relates to 3_ ⁇ -glycosinole and a-trehalose having a trehalose structure, a method for producing the same, and uses thereof.
  • Hi-hi trehalose is a non-reducing disaccharide in which two molecules of glucose are bonded by an a-1, 1 bond, and a small amount of fungi, yeast, bacteria, mushrooms, higher plants, insects, etc. It is widely found in the natural world. Because of its non-reducing properties, it does not cause a Maillard reaction (aminocarbonyl reaction) with substances having an amino group, such as amino acids or proteins, and does not impair the amino acid-containing substance, and is itself stable. Since it is a carbohydrate, it can be used and processed without concerns about browning and deterioration, and a wide range of uses has been expected.
  • Maillard reaction aminocarbonyl reaction
  • a, a _ trehalose Gunorekosu is a _: L, 2 oligosaccharide information about having the structure added with a bond, for example, by a transition operation of the trehalose phosphorylase La one peptidase and Koji cellobiose phosphorylase, arsenic, arsenic - 2-O-a-darcosyl and a-trehalose (also known as a-codibiosyl a_D_dalcoside or seraginose) formed from trehalose are disclosed in Japanese Patent Application Laid-Open No. 10-304882 and Chaen, "Journal of Applied Glycoscience loumal". of Applied Glycoscience) ”, (Saying book), 1999, Vol. 46, No. 4, pp. 423-42 It is described on page 9.
  • Oligosaccharides having a structure in which malto-oligosaccharides such as maltose and maltotriose are added to ⁇ , ⁇ -trehalose by four bonds are described in, for example, European Patent Application Publication No. 06 06753 ⁇ 2, in which starch or a starch moiety is used.
  • A-Trehaloses having a trehalose structure at the terminal a -trehaloses, for example, 4-a-D-gnorecosinole, ⁇ -trehalose, 4-hi-manoletocinore, and hi-trenoose, 4 —Hi-Manoletotori, Shin-Hi-Toreno-guchi, 4-Hi-Malt-tetraosyl-Hi, Hi-I-Trehalose, etc. are disclosed.
  • ⁇ -maltosyl ⁇ _D-gnorecoside ⁇ -maltositol ⁇ -D-gnorecoside, ⁇ -D-gunorecoside, ⁇ -manoletocinore ⁇ - produced from a, a trehalose and cyclomaltohexaose by the transglycosylation of glucanotransferase (CGTase)
  • CGTase glucanotransferase
  • the lipase is formed from dextran and sperm and trehalose by the transfer action of isomanoletodextranase of Arthrobacter globiformis T6. , Shed - "(... Biosci Biotech Biochem) Bioscience Biotechnology Roh I Oh chemistry” iso Marutotorioshinorehi -D- Gunorekoshido is disclosed, also, Kurimoto,, (Japan), In 1997, Vol. 61, No. 4, pp. 699-703 and JP-A-8-217784, there is a description that ⁇ , 1-trehalose is produced by the transfer action of Aspergillus niger's human darcosidase. ⁇ -Isomaltosyl 1D-isomaltoside produced from maltotetraose is disclosed.
  • oligosaccharides having a _1,3 gnorecoside bond include nigrose, which is a reducing disaccharide in which two glucose molecules are _1,3 linked, and glucose at the non-reducing terminal dalcos residue of maltooligosaccharide.
  • Nig-mouth oligosaccharides having a structure added by 1,3 bonds see JP-A-7-59559 and JP-A-9-299095.
  • JP-A-7-59559 and JP-A-9-299095 As disclosed in Japanese Patent Application Laid-Open No. 9-52834, it is known that a carbohydrate containing nigrose as a constituent unit has a high immunostimulating effect in addition to a function as a sweetener such as low sweetness and improved taste quality.
  • both nigerose and nigerooligosaccharide are reducing carbohydrates, and have the disadvantage that they tend to undergo a browning reaction with amino acids and are liable to cause deterioration and deterioration in
  • the present invention relates to a novel carbohydrate having a structure of 3_hi-darcosylhi, hi-trehalose represented by the chemical formula 1 in the molecule, 3_hi-glycosinole, and hy-trehalose (hereinafter simply referred to as "3_ Abbreviations for ⁇ - ⁇ - ⁇ -trehalose ”) and a method for producing the same, and the use thereof will be provided.
  • the present inventors have diligently studied novel carbohydrates 3_ ⁇ _glycosinolehi, hi-treno, and loins and methods for producing the same to solve the above problems.
  • the new Carbohydrate 3-a-isomaltocinole ⁇ , a-trehalose and a novel carbohydrate 3- ⁇ -darcosinolehi, ⁇ -trehalose represented by the chemical formula 3 were found, and further carbohydrates were bound to these new carbohydrates.
  • various other 3_ ⁇ -glycosyl ⁇ , ⁇ - tore /, and oral sugars can be easily synthesized, and that the carbohydrates containing these 3-hydroxyglycosyl and titanium trehaloses can be easily synthesized.
  • the present invention was completed by establishing a method for producing the same.
  • the present invention was completed by establishing compositions such as foods and drinks, cosmetics, and pharmaceuticals containing these saccharides or saccharide compositions containing these saccharides.
  • the 3-a-glycosyl a, a-trehalose of the present invention is a novel carbohydrate that has hitherto been unknown, and is a non-reducing carbohydrate having both a, a_trehalose structure and nigerose structure in the molecule. It is a carbohydrate that can be expected to have various functions.
  • the present invention which provides 3_a-glycosyl a, a-trehalose, a method for producing the same, and a use thereof is a useful invention which greatly contributes to the art.
  • FIG. 1 is a diagram showing 1 H-NMR spectrum of a purified transfer sugar A product.
  • FIG. 2 is a view showing a 13 C-NMR spectrum of a purified transfer sugar A.
  • FIG. 3 is a view showing the structure of 3-a-isomaltosyl a and a-trehalose.
  • FIG. 4 is a diagram showing a 1 H-NMR spectrum of a purified partially decomposed product B.
  • FIG. 5 is a view showing a 13 C-NMR spectrum of a purified partially decomposed product B.
  • FIG. 6 is a view showing the structure of 3_a_darcosyl a, heart trehalose.
  • a, b, c and d mean glucose residues, and correspond to gnorecose residues a, b, c and d in Tables 4 and 6.
  • 3_hyperglycosyl spike, hytrehalose refers to all carbohydrates having a 3-hyrudarcosyl spike, or hypertrehalose structure represented by the chemical formula 1 in the molecule, It is a non-reducing carbohydrate that has both a hy-trehalose structure and a nigrose structure in its molecule.
  • the 3_ ⁇ _glycosyl ⁇ , ⁇ trehalose of the present invention can be obtained from any source or manufactured as long as it is a saccharide having the 3_ ⁇ _darcosyl ⁇ , ⁇ trehalose structure represented by the chemical formula 1 in the molecule. It is not limited by the method, and if it exists as a natural product, it may be of natural origin, or may be chemically or enzymatically synthesized.
  • 3_ ⁇ -isomaltosyl ⁇ , ⁇ -trehalose represented by Chemical Formula 2 (hereinafter, simply referred to as “3- ⁇ -isomaletosyl ⁇ , ⁇ _trehalose”) and 3_ ⁇ -Gnorecocorole ⁇ , represented by Chemical Formula 3 Hi-trehalose (hereinafter simply referred to as “3- ⁇ -gnorecocorole ⁇ , ⁇ -trehalose”) is a specific example of a carbohydrate contained in the above-mentioned 3a-glycosinole ⁇ , trehalose, both of which are different. .
  • the 3_-isomaltosyl spike and the hy-trehalose of the present invention can be chemically synthesized, but the sugar is such that the isomaltose is linked to the spike-and-trehalose by the enzymatic reaction. It is preferable to form by transfer.
  • 3_-isomaltosinole and / or -trehalose by enzymatic reaction for example, panose (4-his-isomaltosyl D-gnorecose), 4_hi-isomaltosyl maltose, 4_hi-isomaltosyl A carbohydrate having a 1,6 gnorecoside bond as a non-reducing terminal binding mode, such as maltotriose, and a 1,4-darcoside bond as a bonding mode other than the non-reducing terminal, and having a glucose polymerization degree of 3 or more.
  • Bacillus globisporus C9 Bacillus globisporus C9, accession number FERM BP-7143
  • Bacillus globisporus Cl 1 Bacillus globisporus C11, accession number FERM BP_7144
  • Bacillus' glo Suporusu N75 Bacillus Globisporus N75, accession number FERM BP-7591
  • a-somaltosyl darco by the action of a microorganism-derived ⁇ -isomaltosyltransferase such as Arthrobacter globiformis A9 (Accession number FERM BP-7590).
  • Hi-trehalose it is preferable to use a commercially available product of the sprout and the heat-trehalose used in the present invention.
  • commercially available products of Hi-trehalose high-purity hydrous crystalline Hi-Hihalose (available from Hayashibara Shoji Co., Ltd., registered trademark “Treha”,, Hi-trehalose content 98% or more) can be advantageously used.
  • a known method for example, extraction from yeast, power to separate from a culture solution of bacteria having the ability to produce spermatozoa, and human trehalose, or whether the enzyme acts on starch can be used. It is also advantageous to use a sponge prepared by the above method.
  • panose As the ⁇ -isomaltosyldarco saccharide used in the present invention, commercially available reagent grade panose (available from Hayashibara Biochemical Laboratory Co., Ltd.) can be used. If necessary, panose can also be prepared by a known method, for example, by reacting a natural polysaccharide pullulan with a panose-forming monoamylase derived from a microorganism such as Thermoactinomyces vulgaris. In addition, Aspergillus niger, Aspergillus awamori, Aspergillus awamori, Aspergillus saitoi, and Muconoleus javanica, which can convert 4 gnorecoside bonds into 6 darcoside bonds.
  • Penicillium 'Talisosgenum' (Pemcillium crysogenum), Canaida 'Trobie squirrel (Candida tropicalis) and a human darcosidase derived from microorganisms are applied to starch to make panose, 4_hi-isomanolet sill maltose, 4_hi-iso It is also possible to prepare human isomaltosylglycosides, such as maltosylmaltotriose, etc. Furthermore, the applicant has disclosed Bacillus' globisporus C9 (Bacillus globisporus C9) disclosed in International Patent Application Publication WO 02/055708 A1.
  • 3_H-isomaltosyl-hyper-trehalose is usually produced by adding an isomaltosyltransferase to an aqueous solution containing y-hyper-trehalose and hyper-isomaltosyldarcosaccharide.
  • One unit of the activity of polysomaltosyltransferase used in the present invention is an enzyme that produces 1 ⁇ mol of gnorecose per minute under the conditions of 30 ° C. and pH 6.0 using lwZv 0 / ° C as a substrate. Defined as quantity.
  • this enzyme reaction solution along with 3_-i-isomaretosinole and 1-trehalose, an oligosaccharide having one or several ⁇ - 1,3 linkages of the i-iso-manoletosyl group is formed. .
  • This reaction solution usually contains reducing sugars such as gnorecose and maltooligosaccharides, cyclo ⁇ 6) _a_D—darcoviranosyl (1 ⁇ 3) —a—D—dalcoviranosyl (1 ⁇ 6) ) —A—D-Darcopyrano siro (l ⁇ 3) _a_D—Cyclic tetrasaccharide having the structure of gnorecopyranosyl- (1 ⁇ ) (hereinafter simply referred to as “cyclic tetrasaccharide” in the present specification). ), Unreacted ⁇ , ⁇ -trehalose and the like.
  • the 3_ ⁇ _darcosyl ⁇ , ⁇ -trehalose of the present invention can be chemically synthesized.
  • the 3_ ⁇ -isomaltosyl ⁇ , ⁇ -trehalose-containing solution produced above and the dalcosyl By acting on amylase (EC 3.2.1.3) to specifically cleave the 1,6-gnorecoside bond of 3_ ⁇ -isomaltosyl ⁇ , ⁇ -trehalose, it can be easily formed.
  • the dalcoamylase used in the preparation of 3-hidalchosinore and trehalose from 3hi-isomaltosylhi and trehalose is easily hydrolyzed with a 1,6-darkosyl bond.
  • Any enzyme that decomposes and does not easily hydrolyze the 1,3 gnorecosyl bond can be used.
  • darcoamylase derived from microorganisms such as Aspergillus niger, Rhizopus niveus, etc. is advantageously used. it can.
  • One unit of the activity of the dalcoamylase used in the present invention was defined as the amount of enzyme which produces 10 mg of gnorecose in 30 minutes at 40 ° C and pH 4.5 using lwZv% soluble starch as a substrate.
  • 3-saccharides and trehalose are formed together with one or more oligosaccharides, which are linked by one or a few 1,6-bonds, to the lignin and trehalose.
  • the reaction solution usually contains reducing saccharides such as dalcose and nigrose, cyclic tetrasaccharides, unreacted spikes, and hypertrehalose.
  • the aqueous solution containing 3_-isomaltosyl spike, hy-trehalose and Z or 3-hi-darcosyl a, ⁇ -trehalose of the present invention is subjected to a sugar transfer reaction using an appropriate saccharide and the saccharide donor as a sugar donor.
  • 3_ ⁇ -isomaltosyl isomaltosyl residue of ⁇ -trehalose or 3_ ⁇ -darcosyl
  • galactose When lactose is reacted with / 3_galactosidase, galactose is added to the isomaltosyl residue of 3_a-isomaltosyl and a-trehalose, or to the darcosyl residue of 3_hy-darcosyl and trehalose.
  • galactose in addition to glucose as a constituent sugar
  • Heterogeneous 3_ ⁇ -glycosyl ⁇ , ⁇ -trehalose can also be enzymatically synthesized.
  • the 3 ⁇ -glycosyl ⁇ , ⁇ trehalose-containing solution produced by the enzymatic reaction as described above usually contains 3 to 15 w / w of 3_ ⁇ -glycosinole ⁇ , ⁇ -trehalose per solid. % (Hereinafter, in this specification, unless otherwise specified.
  • The which may be filtered and purified and used in liquid or syrup form, or dried and used in solid form.
  • the above-mentioned solution is further separated and purified to make use of the characteristics of 3_hyperglycosyl and / or trehalose in order to take advantage of the characteristics of 3_hyperglycosyl and / or trehalose. It can also be used as a product.
  • a method of separation and purification for example, a method of separating and removing contaminating saccharides by a yeast fermentation method, a membrane filtration method, a fractional precipitation method, an alkali treatment method, column chromatography, or the like can be appropriately employed.
  • contaminant saccharides are removed by column chromatography using salt type strongly acidic cation exchange resin disclosed in JP-B-62-50477, JP-B-4-50319, etc.
  • the method of collecting fractions can be advantageously implemented. At this time, it is optional to adopt any of the fixed bed system, the moving bed system, and the simulated moving bed system.
  • 3-a-glycosyl ⁇ , a trehalose-containing saccharide is hydrogenated according to a conventional method, and the reducing saccharides such as gnorecose and maltose contained therein are converted into saccharide alcohol. It is also possible to advantageously carry out the production of 3- ⁇ -glycosyl ⁇ , ⁇ -trehalose-containing saccharides which lose the reducing power and exhibit substantially no reducibility.
  • the 3 ⁇ -glycosyl ⁇ , ⁇ trehalose of the present invention is itself non-reducing, extremely stable, has a low sweetness but a good and mild sweetness, Amino acids and oligopeptides, which are prone to browning reaction with saccharides, as well as active ingredients and biologically active substances that are liable to lose their activity. It has properties such as properties, moisturizing properties, viscosity, anti-crystallization properties of other saccharides, poor fermentation properties, and anti-aging property of starch.
  • 3-a-glycosinole and a-trehalose are considered to be various compositions such as foods and drinks, taste foods, feedstuffs, foodstuffs, foods and drinks, and further cosmetics and pharmaceuticals. It can be used advantageously for products. Above all, 3_glycosinoles and trehaloses are It is also advantageous to produce various compositions by incorporating them together with one or more components selected from reducing oligosaccharides, reducing oligosaccharides, sugar alcohols and minerals.
  • the 3_ ⁇ -glycosyl ⁇ , ⁇ -trehalose-containing saccharides of the present invention and the 3_-glycosyl spices and the high-trehalose-rich contents obtained therefrom can be directly used as a seasoning for sweetening. Can be used.
  • starch syrup glucose, maltose, hi, hi-trehalose, sucrose, ratatosucrose, isomerized sugar, honey, maple sugar, sorbitol, maltitol, ratatitol, dihydrochalcone, stevioside, hi-glycosi
  • it may be used in admixture with an appropriate amount of one or more other sweeteners such as rustebioside, rebaudioside, glycyrrhizin, L-aspartyl-L-phenylualanine methyl ester, saccharin, glycine, alanine, etc.
  • it can be used in admixture with fillers such as dextrin, starch, lactose and the like.
  • the powdery product of the present invention containing 3_-glycosyl paraffin, human trehalose-containing saccharides and 3_ ⁇ -glycosinole ⁇ , ⁇ -trehalose-rich substances obtained therefrom can be used as it is.
  • the composition may be mixed with a bulking agent, excipient, binder, or the like, and molded into various shapes such as granules, spheres, short rods, plates, cubes, and tablets.
  • the sweetness of the 3_ ⁇ _glycosyl ⁇ , ⁇ -trehalose-containing saccharide of the present invention and the 3_ ⁇ -glycosyl ⁇ , ⁇ -trehalose-rich content obtained from the saccharide include acidity, salty taste, It harmonizes well with various substances having other tastes such as astringency, umami, and bitterness, and has high acid resistance and heat resistance, which is advantageous for sweetening and improving the taste and taste of general foods and drinks. Available.
  • soy sauce, powdered soy sauce, miso, powdered miso, moromi, hishio, sprinkle, mayonnaise, dressing, vinegar, three tablespoon vinegar, powdered sushi vinegar, chinese noodles, tentsuyu, potsuyu, sauce, kechiyap, takuan pickle
  • seasonings such as raw ingredients, Chinese cabbage pickles, grilled meat sauce, curry ⁇ , stew ingredients, soup ingredients, dash ingredients, complex seasonings, mirin, new mirin, table sugar, coffee sugar, etc.
  • various Japanese confectionery such as rice crackers, hail, rice bran, rice cakes, steamed buns, seaweeds, bean jam, yokan, mizuyokan, nishikidama, jelly, castella, candy, bread, biscuits, crackers, cookies , Pie, pudding, butter cream, custard cream, cream puff, puff Paste, sponge cake, donut, chocolate, chewing gum, caramel, candy such as candy, ice cream, ice confectionery such as sorbet, fruit syrup pickling, syrup such as ice honey, flower paste, peanut paste, fruit paste, spread, etc.
  • Fruits such as pastes, jams, marmalades, syrup pickles, sugar cane, processed foods of vegetables, pickles such as Fukujin pickles, bettarazuke, senmai pickles, ratsuyo pickles, meat products such as ham and sausage, fish ham, Fish meat products such as fish sausage, power, maboko, chikuwa, tempura, various delicacies such as sea urchin, salted squid, vinegared konbu, sakisume, dried fugumirin, seaweed, wild vegetables, sardines, small fish, shellfish And other prepared foods such as tsukudani, boiled beans, potato salad, konbu rolls, etc.
  • pickles such as Fukujin pickles, bettarazuke, senmai pickles, ratsuyo pickles, meat products such as ham and sausage, fish ham, Fish meat products such as fish sausage, power, maboko, chikuwa, tempura, various delicacies such as
  • feed and the like for domestic animals, poultry, and other bred animals such as bees, silkworms, and fish.
  • various solids such as tobacco, toothpaste, lipstick, lip balm, oral liquid, tablets, troches, liver oil drops, mouth fresheners, mouth fragrances, gargles, etc. It can be advantageously used as a sweetener for various compositions such as, for example, as a taste improver, a flavor enhancer, and as a quality improver.
  • compositions are made to contain 3_-glycosyl sp, trehalose-containing saccharides or 3_-glycosyl sp, and high trehalose-rich substances obtained from the saccharides.
  • the method can be selected as long as it is included in the process until the product is completed.A known method such as mixing, dissolving, melting, dipping, penetrating, spraying, coating, coating, spraying, pouring, and solidifying is appropriately selected. .
  • the amount is usually 0.1% or more, preferably 0.5% or more.
  • the solution was sterilized in an autoclave at 121 ° C for 20 minutes, cooled, inoculated with Bacillus' Globisporus C11 strain, and cultured with rotation and shaking at 230 rpm at 27 ° C for 48 hours to obtain a seed culture.
  • a medium of the same composition as in the case of seed culture is placed in a 30-L fermenter, heat-sterilized, cooled to a temperature of 27 ° C, and inoculated with 1% (v / v) of the seed culture solution.
  • the culture was aerated and agitated for 48 hours while maintaining the temperature at 27 ° C and pH 6.0 to 8.0.
  • the enzymatic activity in the culture was measured and found to be about 0.55 units / ml for iso-isomaltosyldarco saccharide-forming enzyme and about 1.8 units / ml for para-isomaltosyltransferase.
  • the culture was harvested by centrifugation (10,000 rpm, 30 minutes) When the enzyme activity of about 18 L was measured, ⁇ -isomaltosinolegnoreco saccharide-forming enzyme activity was about 0.51 units / ml (total activity of about 9,180 units), and ⁇ -isomaltosyltransferase activity was about 1.7 units / ml (total activity about 30,400 units).
  • the activities of the two enzymes were measured as follows. That is, measurement of the specific one Isomarutoshirugu Turkey saccharide-forming enzyme activity, maltotriose concentration 2% (w / v) and made as 100 mM acetate buffer and (P H6. 0).
  • the substrate Add 0.5 ml of the enzyme solution to 0.5 ml of the solution, carry out the enzyme reaction at 35 ° C for 60 minutes, boil the reaction solution for 10 minutes to stop the reaction, and then increase the maltose content in the reaction solution at high speed.
  • the determination was performed by liquid chromatography (hereinafter abbreviated as "H PLC").
  • One unit of the activity of the enzyme producing isomaltosyldarco saccharide is defined as the amount of the enzyme that produces 1 ⁇ mol maltose per minute under the above conditions.
  • HPLC was carried out using a Shodex KS_801 column (manufactured by Showa Denko KK), using water as the eluent, at a column temperature of 60 ° C and a flow rate of 0.5 mlZmin. A total of -8012 (manufactured by Tosoichi Co., Ltd.) was used.
  • a measurement of a-isomaltosyltransferase activity was performed by dissolving noose in a 100 mM acetate buffer (pH 6.0) to a concentration of 2% (w / v) to obtain a substrate solution.
  • Add 0.5 ml of the enzyme solution to 0.5 ml of the substrate solution carry out the enzymatic reaction at 35 ° C for 30 minutes, boil the reaction solution for 10 minutes to stop the reaction, and determine the amount of gnorecose in the reaction stop solution with glucose.
  • the determination was performed by the oxidase method.
  • One unit of the activity of ⁇ -isomaltosyltransferase was defined as the amount of enzyme that produced 1 ⁇ mol of glucose per minute under the above conditions.
  • This crude enzyme solution was subjected to ion exchange chromatography using “Sepabeads FP-DA13” gel (manufactured by Mitsubishi Chemical Corporation). Both Hi-isomaltosyldarco saccharogenic enzyme active ingredient and Hi-isomaltosyltransferase active ingredient are referred to as “Sepabeads FP_ Both enzyme activities were detected in the non-adsorbed fraction without adsorbing on the DA13 ′′ gel. The non-adsorbed fraction was collected, dialyzed against 10 mM phosphate buffer (pH 7.0) containing 1 M ammonium sulfate, and the dialysate was centrifuged to remove insolubles.
  • the active ingredient of iso-maltosyltransferase and the active ingredient of iso-isomaltosyl danoreco saccharide-forming enzyme were separated and eluted, and the activity of a- isomaltosinosyltransferase was determined for the fraction with an ammonium sulfate linear gradient concentration of about 0.3M.
  • the enzyme activity of carbohydrate-forming enzyme for isocyanole sinolegnoleco was detected in a fraction having a linear gradient concentration of maltotetraose of about 3 OmM.
  • Experimental Example 11 A partially purified enzyme preparation having ⁇ -isomaltosinolegnoreco saccharide-forming enzyme activity obtained by the method of 1-2 was dialyzed against a 10 mM phosphate buffer ( ⁇ 7.0) containing 1 M ammonium sulfate. Then, the dialysate was centrifuged to remove insolubles, and subjected to hydrophobic chromatography (gel volume: 350 ml) using “Butyl-Toyopear 1 650M” gel (manufactured by Tosoh Ichi Co., Ltd.). Provided.
  • the active ingredient of this enzyme was adsorbed on the “Butyl_Toyopearl” 650M gel and eluted with a linear gradient of ammonium sulfate from 1M to OM.
  • the enzyme adsorbed at an ammonium sulfate concentration of about 0.3M
  • the active component was eluted, and a fraction exhibiting the enzyme activity was collected. Again, the collected fraction was dialyzed against 10 mM phosphate buffer (pH 7.0) containing 1 M ammonium sulfate, and the dialysate was centrifuged to remove insolubles, and then “Sephacryl HR S-200
  • the product was purified using affinity chromatography using a gel. Enzyme having the activity of carbohydrate synthase producing isomaltocinorelegnoleco in each step of this purification Table 1 shows the enzyme activity, specific activity and yield of the sample.
  • the active ingredient of this enzyme was adsorbed on the “Butyl_Toyopearl 650M” gel and eluted with a linear gradient of ammonium sulfate from 1M to 0M, and eluted at about 0.3M ammonium sulfate.
  • the fractions exhibiting the present enzyme activity were collected and collected. Again, this recovered solution was dialyzed against 10 mM phosphate buffer (pH 7.0) containing 1 M ammonium sulfate, and the dialysate was centrifuged to remove insolubles, and “Sephacryl HR S_200” gel was used. Purified using affinity chromatography. Table 2 shows the enzyme activity, specific activity and yield of the enzyme preparation having monoisomaltosyltransferase activity in each step of this purification.
  • the generated transfer sugar ⁇ ⁇ is presumed to be 3_a-isomaltosyl and a-trehalose having a structure in which three ⁇ -isomaltosyl residues are bonded to ⁇ , ⁇ -trehalose.
  • HPLC was performed by using two "MCI GEU CK04SS columns” (manufactured by Mitsubishi Chemical Corporation) connected in series. The column temperature was determined using water as the eluent. The detection was performed using a differential refractometer “RI-8012” (manufactured by Tosoh Corporation) at 80 ° C. and a flow rate of 0.4 ml / min.
  • the preparative HPLC was carried out using an “ODS-AQ (ODS-AQ) R355-15AQ column” (manufactured by YMC Corporation) using water as the eluent at a column temperature of 25 ° C and a flow rate of 20 ml / min.
  • the detection was performed using a differential refractometer “ERC_7530” (manufactured by Elma Optics Co., Ltd.).
  • isomalt dextranase treatment was performed. That is, the partially purified transfer sugar A After adjusting the pH of the aqueous solution to 5.0 and the temperature to 50 ° C, and treating the isomaltodextranase from Arthropactor 'Globiformis' at 1,000 units per gram of solid matter, treating at 50 ° C for 24 hours, The enzyme was inactivated by heating at 100 ° C. for 10 minutes, and the enzyme treatment was stopped. The obtained treatment liquid was desalted and concentrated to obtain 3.4 g of a treated substance as a solid.
  • Transferred sugar A and isomaltose in the obtained processed product were separated by the above-mentioned preparative HPLC, and a fraction containing transferred sugar A was recovered. 6 gram of purified transferase A was obtained. Analysis by HPLC revealed that the sugar content of the transferred sugar A was 99.9% or more, indicating that it was a very high-purity transferred sugar A sample.
  • the purified transfer sugar A obtained by the method of Experimental Example 3 was subjected to mass spectrometry by electrospray ionization using a mass spectrometer “LCQ Advantage” manufactured by Thermo Electron, Ltd. Was remarkably detected, and the mass number of the present saccharide was found to be 666.
  • the purified transfer sugar A obtained by the method of Experimental Example 3 was hydrolyzed with sulfuric acid according to a conventional method, and the constituent sugars were examined by gas chromatography.D-Gnorecose alone was detected, and The constituent sugar was found to be D-glucose.
  • the purified transfer sugar A obtained by the method of Experimental Example 3 was methylated according to a conventional method, hydrolyzed with an acid, then reduced and acetylated, and the obtained partial methyl hexitol acetate was subjected to gas chromatography. I checked by law.
  • transfer sugar A was a saccharide having the structure shown in FIG. 3, that is, 3_ ⁇ -isomaltosyl ⁇ , ⁇ -trehalose represented by chemical formula 2.
  • aqueous solution having a sugar concentration of 2% and a pH of 4.5 was prepared using about half (0.8 g as a solid) of purified 3_-isomaltosyl sp. And purified human trehalose obtained by the method of Experimental Example 3. Then, add 3,000 units of gnorecoamylase (trade name “Darco Team # 12000”, sold by Nagase Seikagaku Co., Ltd.) per gram of solids, react at 50 ° C for 24 hours, and react at 100 ° C for 10 hours. The reaction was stopped by heating for minutes to inactivate the enzyme. The obtained reaction solution was filtered, desalted, and analyzed by HPLC. Table 5 shows the results of the HPLC.
  • the resulting partially degraded product a is composed of a, trehalose and 3-, 1-glucosinole and Estimated.
  • glucose was eluted at an elution time of about 34 to 48 minutes
  • the partially decomposed product B was eluted at an elution time of about 44 to 48 minutes.
  • Unreacted 3_ ⁇ -Isomaletosyl ⁇ , ⁇ _trehalose eluted at an elution time of 53 to 60 minutes.
  • the fraction containing the partially decomposed product was collected, filtered and concentrated to obtain 0.49 g of a partially decomposed product as a solid.
  • the partially decomposed product was found to have a sugar composition of 99.9% or more, indicating that the product was an extremely high-purity partially degraded product sample.
  • the acetate was examined by gas chromatography.
  • the ratio of 2,3,4,6-tetramethyl-1,5-diacetyldarcitol to 2,4,6-trimethyl-1,3,5-tetraacetinole gnoresitol was 2.1: 1.0.
  • the present carbohydrate was found to be composed of two molecules of glucose residues involved in binding at position 1 and one molecule of glucose residues involved in binding at positions 1 and 3.
  • the partially degraded product B was a carbohydrate having the structure shown in FIG. 6, that is, 3_hydarkosylhi and hytrehalose represented by Chemical Formula 3.
  • Examples 1 to 8 the methods for producing 3_ ⁇ -glycosyl ⁇ , ⁇ -trehalose and the saccharide containing the same according to the present invention will be described in Examples 1 to 8, and the 3- ⁇ -glycosyl ⁇ , ⁇ trehalose and the method for producing the same will be described.
  • Examples 9 to 19 show compositions containing saccharides.
  • Trehalose Hayawara Shoji Co., Ltd., registered trademark “Treha”
  • Panose manufactured by Hayashibara Biochemical Research Laboratories
  • the reaction solution is heated to 95 ° C and maintained for 10 minutes, then cooled, filtered, and the filtrate obtained is decolorized with activated carbon and desalted with H-type and OH-type ion exchange resins according to a conventional method for purification. Then, the mixture was concentrated, dried and pulverized to obtain a powder containing 3_-isomaltosyl and / or trehalose in a yield of about 91% per solid.
  • This product is composed of 8.0% glucose, a, 66.3% a, trehalose monosaccharide, 13.9% 3_hymani somanoletocinole, and 13.9% cyclotetrasaccharide, 6.0% cyclic tetrasaccharide per solid. And 5.8% of other carbohydrates, and has mild sweetness, moderate viscosity, moisturizing properties, inclusion properties, sweeteners, taste improvers, quality improvers, water separation inhibitors, As a stabilizer, excipient, clathrate, powdered base material, etc., it can be advantageously used for various compositions such as various foods and drinks, cosmetics and pharmaceuticals.
  • the powder containing 3_ ⁇ -isomaltosyl and ⁇ -trehalose obtained by the method of Example 1 was dissolved in warm water and adjusted to a concentration of 60%, and then a strongly acidic cation exchange resin (Amberlite CR-1310, Na type, organo (Manufactured by Co., Ltd.).
  • the resin was packed in four jacketed stainless steel columns having an inner diameter of 5.4 cm and connected in series to make the total resin layer length 2 Om. While maintaining the column temperature at 60 ° C, add 5 v / v% of the sugar solution to the resin, and then fractionate the solution by flowing hot water at 60 ° C with SVO.13, and determine the sugar composition of the eluate by HPLC.
  • the fractions containing 3- ⁇ -isomaltosyl ⁇ , ⁇ -trehalose were collected, desalted, and concentrated, and a 70% concentration of syrup containing 3_ ⁇ -isomaltosyl ⁇ , ⁇ -trehalose was applied to the solid material.
  • the yield was about 16%.
  • This product contains 61.5% of 3_ ⁇ _isomaltosyl ⁇ , ⁇ -trehalose, 38.3% of cyclic tetrasaccharides, and 0.2% of other saccharides per solid, and is reducible. It has a mild sweetness, moderate viscosity, moisturizing property, and inclusion property that hardly cause aminocarbonyl reaction.
  • Sweeteners taste improvers, quality improvers, anti-synthesis agents, stabilizers, excipients, clathrates, powdered base materials, etc., advantageously used in various compositions such as foods, beverages, cosmetics, and pharmaceuticals it can.
  • the syrup containing 3_ ⁇ -isomaltosyl and ⁇ -trehalose obtained by the method of Example 2 was concentrated.
  • the reaction solution is heated to 95 ° C and maintained for 10 minutes, cooled, filtered, and the filtrate obtained is decolorized with activated carbon according to a conventional method, and desalted with H-type and OH-type ion exchange resins. After purification and further concentration to a concentration of 65%, column fractionation using the strongly acidic cation exchange resin described in Example 2 was carried out.
  • the fraction containing 3-hytoisomaltosyl and high trehalose was high.
  • the product contains 98% of 3_hi-isomaltosylhi and hi-trehalose per solid, has substantially no reducibility, and is mildly sweet and less susceptible to an aminocarbonyl reaction. It has moderate viscosity and moisturizing properties, and is used as a sweetener, taste improver, flavor improver, quality improver, syneresis inhibitor, stabilizer, excipient, powdered base material, etc. It can be advantageously used for various compositions such as cosmetics and pharmaceuticals.
  • the 3a-isomaltosyl ⁇ , a trehalose-containing powder obtained by the method of Example 1 was dissolved in warm water, adjusted to a concentration of 10%, a pH of 4.5, and a temperature of 50 ° C, and added to the dalcoamylase agent (Nagase Seikagaku Corporation). (Manufactured by Co., Ltd., trade name “Darco Team”) was added at a ratio of 1 000 units per lg of the solid matter, and reacted for 48 hours.
  • the reaction solution was heated to 95 ° C and kept for 10 minutes, cooled, filtered, and the filtrate obtained was decolorized with activated carbon according to a conventional method, and then purified by desalting with H-type and OH-type ion exchange resins. Then, the mixture was further concentrated to a concentration of 65% to obtain a syrup containing 3_ ⁇ -gnorecosyl ⁇ , ⁇ -trehalose in a yield of about 95% per solid.
  • the product is composed of glucose 14.7%, solids a, trehalose 66.2%, 3-hyun gnorecosinole, trehalose 1-1.0%, cyclic tetrasaccharide 6.0%, And 2.1% of other carbohydrates, and has mild sweetness, moderate viscosity, moisturizing properties and inclusion properties, sweeteners, taste improvers, quality improvers, water separation inhibitors, stable It can be advantageously used for various compositions such as various foods and drinks, cosmetics and pharmaceuticals as agents, excipients, clathrates, powdered base materials and the like.
  • Example 5 Using the 3-a-dalcosyl ⁇ , a-trehalose-containing syrup obtained by the method of Example 4 as a raw material, column fractionation was carried out using the strongly acidic cation exchange resin described in Example 2 to give 3- ⁇ - The fraction containing high gnorecosyl ⁇ , hy-trehalose content was collected, desalted, concentrated, dried, and pulverized to obtain a powder containing high content of 3_hyuno-genorecosinole and high trehalose, about 6% yield per solid. I got it.
  • the product contains 98% of 3-hidarcosylhi and hi-trehalose per solid, has substantially no reducibility, and has a mild low sweetness that is less susceptible to the aminocarbonyl reaction. It has a suitable viscosity and moisturizing properties and is used as a sweetener, taste improver, flavor improver, quality improver, syneresis inhibitor, stabilizer, excipient, powdered base material, etc. It can be advantageously used for various compositions such as cosmetics and pharmaceuticals.
  • a-Il-trehalose (trade name “Treha”, sold by Hayashibara Shoji Co., Ltd.) and starch milk containing tapio power starch at a concentration of about 12.5%, respectively, were added to this, and they were combined with para-amylase (trade name “Neospitase”). , Nagase Seikagaku Kogyo Co., Ltd.) at 0.2% per gram of starch solids, react at 85-90 ° C for about 20 minutes, then autoclave at 120 ° C for 20 minutes, and further heat to about 35 ° C.
  • the mixture was rapidly cooled to obtain a liquefied solution containing about 2 DE and a mixture of trehalose, and the above concentrated enzyme solution was added thereto at a ratio of 0.3 ml per gram of solid starch, pH 6.0, and a temperature of 35 ° C.
  • the reaction was performed at C for 48 hours.
  • the reaction solution was kept at 95 ° C for 30 minutes, cooled, filtered, and the resulting filtrate was decolorized with activated carbon, desalted with H-type and ⁇ H-type ion exchange resins, and purified according to a conventional method.
  • the concentrate was further concentrated to obtain a syrup containing 70% of 3_-isomaltosyl and trehalose in a yield of about 90% based on the solid material.
  • This product is composed of, per solid, glucose 2.7%, a, trehalose 40.2%, soybean trehalose, trehalose 18.2%, 9.8% cyclic tetrasaccharide , And 29.1% of other carbohydrates, and has mild sweetness, moderate viscosity, moisturizing properties, inclusion properties, sweeteners, taste improvers, quality improvers, and water separation inhibitors , Stabilizers, excipients, clathrates, powdered base materials, etc.
  • it can be advantageously used for various compositions such as various foods and drinks, cosmetics, and pharmaceuticals.
  • the syrup containing 3a isomaltosyl ⁇ , a trehalose obtained by the method of Example 6 was adjusted to a concentration of 30%, pH 4.5, and a temperature of 50 ° C, and added to the darcoamylase agent (manufactured by Nagase Seikagaku Corporation). (Gnoreco team) was added at a rate of 1,000 units per lg, and reacted for 48 hours.
  • the reaction mixture was heated to 95 ° C and maintained for 10 minutes, cooled, filtered, and the filtrate obtained was decolorized with activated carbon and desalted with H-type and H-type ion exchange resins according to a conventional method.
  • the reducing sugar was converted to a sugar alcohol by hydrogenation according to a conventional method, and again decolorized, desalted, concentrated, dried, and pulverized to obtain 3- ⁇ -Darcosine.
  • the trehalose-containing powder was obtained at a yield of about 85% per solid
  • This product is composed of 13.3% of sonorebitonore per solid, a, 42.1% of trehalose, 1_ darcosinole ⁇ , 13.7% of trehalose, 9.9% of cyclic tetrasaccharide, And 16.0% of other sugar alcohols, etc., exhibit substantially no reducing properties, and have mild sweetness, moderate viscosity, moderate viscosity, As a sweetener, taste improver, quality improver, syneresis inhibitor, stabilizer, excipient, clathrate, powdered base material, etc., for various compositions such as various foods, beverages, cosmetics, and pharmaceuticals It can be used advantageously.
  • the reaction solution was kept at 95 ° C for 30 minutes, cooled, filtered, and the filtrate obtained was decolorized with activated carbon according to a conventional method, and purified by desalting with H-type and OH-type ion exchange resins.
  • the concentrated syrup containing 70% 4- ⁇ -galatatosyl-3-a-glucosinole and a -trehalose was obtained at a yield of about 90% per solid material.
  • This product is composed of 22.7% glucose, 3.4% galactose, 5.9% lactose, 3_ 1g gnorecosinole, 35.1% trehalose, and 3 ⁇ -galactosinole 3 per solid.
  • _Hiichi Gunorekoshinore Contains 13.5% of a, ⁇ -trehalose and 19.4% of other saccharides, has mild sweetness, moderate viscosity and moisturizing properties, sweetener, taste improver, and quality improvement It can be advantageously used for various compositions such as various foods and drinks, cosmetics and pharmaceuticals as agents, anti-separation agents, stabilizers, excipients, and powdered base materials.
  • a-trehalose-containing material obtained by the method of Example 6 was mixed with 100 parts by mass of a 55% sucrose solution under heating, and then the water content was reduced to less than 2% under reduced pressure.
  • the mixture was concentrated by heating to a concentration of 0.6 part by weight of cunic acid, mixed with an appropriate amount of a lemon flavor and a coloring agent, and molded according to a conventional method to obtain a product.
  • This product is a stable, high quality hard candy with good crispness, taste and flavor, no sucrose crystallization, and low hygroscopicity.
  • Example 12 3 parts by weight of the gum base were heated and melted to a degree to be softened, and 2 parts by weight of anhydrous crystalline multitol, 2 parts by weight of xylitol, and syrup-like 3_hydarcosil and hytrehalose obtained by the method of Example 4 were added. 3 parts by mass of the product were mixed together, and an appropriate amount of a fragrance and a coloring agent were further mixed, kneaded by a roll, molded and packaged according to a conventional method to obtain a product. This product has good texture, good taste and good taste, and is suitable as a chewing gum with low caries and low calories. [0097] Example 12
  • soy peptide solution for foods (trade name "Hi-New II", sold by Fuji Oil Co., Ltd.) 1 part by mass of syrup-like 3-hyto-isomaltosyl-hypy, hy-trehalose obtained by the method of Example 2 Two parts by mass of the ingredients were mixed, placed in a plastic vat, dried at 50 ° C. under reduced pressure, and pulverized to obtain a powdered peptide.
  • This product has a good flavor and is useful not only as a low-calorie confectionery material for premixes and frozen desserts, but also as an indigestible dietary fiber, an intestinal material, and a health food material for oral liquid foods and tube liquid foods. It is also useful.
  • This product has a rich scent of uzu, and it can be diluted 100 to 10,000 times in hot water for bathing. After bathing, the skin is moist and smooth, and high quality that does not cool down Bath agent.
  • Toothpaste was obtained by mixing 13 parts by mass of a material containing heat trehalose, 0.02 parts by mass of saccharin and 0.05 parts by mass of a preservative with 15 parts by mass of water. This product improves the taste of surfactants without reducing their detergency and gives a good feeling after use.
  • a formulation consisting of 0.6 parts by mass of acetate and 0.04 parts by mass of nicotinamide was prepared, and 25 g each of this formulation was filled into a moisture-proof laminate sachet and heat-sealed to obtain a product.
  • the product is a liquid edible solid preparation having excellent stability.
  • One bag of this product is dissolved in about 150 to 300 ml of water to make a liquid diet, and is used orally or by tube application to the nasal cavity, stomach, intestine, etc., and is advantageous for replenishing energy to living organisms Available to
  • a 150 mg uncoated tablet was used as a core, and 40 parts by mass of powdery 3_-his-isomaltosyl a, a-trehalose high content obtained by the method of Example 3 and pullulan (average molecular weight 200,000) 2 mass Parts, water 30 parts by weight, talc 25 parts by weight and titanium oxide 3 parts by weight, sugar-coated until the tablet weight becomes about 230 mg, then 65 parts by weight of cyclic tetrasaccharide crystal powder, pullulan 1 Using an overhanging solution consisting of 34 parts by mass of water and 34 parts by mass of water, sugar-coated tablets were obtained, which were further glossed with a mouth liquid to give an excellent glossy appearance. This product has excellent impact resistance and maintains high quality for a long time.

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Abstract

Cette invention concerne un nouveau glucide qui est un composé de 3-α-glycosyleα, α-tétralose présentant une structure 3-α-glucosyle α, α-tétralose et qui est représenté par la formule (1) dans la molécule.
PCT/JP2004/010225 2003-07-18 2004-07-16 COMPOSE DE 3-$G(A)-GLYCOSYLE$G(A), $G(A)-TETRALOSE, METHODE DE FABRICATION ET UTILISATION WO2005007664A1 (fr)

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GB2420345A (en) 2006-05-24
JP2005035958A (ja) 2005-02-10
US20060183714A1 (en) 2006-08-17

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